C - Chemistry – Metallurgy – 07 – C
Patent
C - Chemistry, Metallurgy
07
C
260/517.1, 260/5
C07C 51/353 (2006.01) C07C 51/347 (2006.01) C07C 53/128 (2006.01) C07C 61/08 (2006.01) C07C 61/13 (2006.01)
Patent
CA 2029899
To produce a carboxylic acid R<1>-COOH, in which R<1> is a tertiary branched alkyl residue or a cylcoalkyl residue with one or more rings, which may be attached, and possibly substituted by at least one alkyl residue, the alpha carbon atom of the carbonyl group being a tertiary carbon atom, a branched or cyclic alkane R<1>H, in which R<1> is a branched alkyl residue or a cycloalkyl residue with one or more rings, which may be attached, and possibly substituted by at least one alkyl residue, the alpha carbon atom of the hydrogen atom being a tertiary carbon atom or a secondary carbon atom capable of being rearranged during reaction to a tertiary atom, is reacted in the presence of an acid catalyst with a formiate H(CO)O(CR<2>R<3>R<4>), in which R<2>, R<3> and R<4> denote hydrogen or alkyl, under the three following conditions: that R<2>, R<3> and R<4> are not simultaneously hydrogen; that the formiate yields, in the reaction medium, directly or following a rearrangement, a stable R<2>R<3>R<4>C<+> cation; and that the alkane R<2>R<3>R<4>CH formed can be easily eliminated from the reaction medium.
PRECIS DE LA DIVULGATION: Pour fabriquer un acide carboxylique R1-COOH, avec R1 = reste alkyle ramifié tertiaire ou bien reste cycloalkyle à un ou plusieurs cycles, accolés ou non, et éventuellement substitué par au moins un reste alkyle, l'atome de C en alpha du groupe carbonyle étant un atome de C tertiaire, on fait réagir, en présence d'un acide comme catalyseur, un alcane ramifié ou cyclique R1H, avec R1 = reste alkyle ramifié ou bien reste cycloalkyle à un ou plusieurs cycles accolés ou non, et éventuellement substitua par au moins un reste alkyle, l'atome de C en alpha de l'atome d'hydrogène étant un atome de C tertiaire ou un atome de C secondaire capable de se réarranger en cours de réaction en atome tertiaire, avec un formiate H(CO)O(CR2R3R4), R2, R3 et R4 = H ou alkyle, à la triple condition que R2, R3 et R4 ne soient pas simultanément H, que le formiate conduise dans le milieu réactionnel, directement, ou à la suite d'un rèarrangement, à un cation R2R3R4C + stable, et que l'alcane R2R3R4CH qui se forme puisse s'éliminer aisément du milieu réactionnel.
Gallo Roger
Jalal Rachid
Lazzeri Veronique
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